Anal penetration and pegging (Page 2)

You can always tell how interested I am in sex by what I write. I’m sure I will not shock you if I tell you that I’ve been thinking about sex. Even though we are celebrating Unlocktober, we haven’t quite kept up with our every-other-day pace of orgasms. Saturday night, we started late and while Mrs. Lion worked valiantly pumping my penis with her hand, I got very hard but I just couldn’t get past that plateau. She’s resolved to keep trying.

Meanwhile, my thoughts have been drifting rearward. My antasies are remembrances of my own anal experiences. For a while, Mrs. Lion was working to expand, so to speak, my anal horizon. She was using a combination of fingers, butt plugs, and ever-increasing-in-diameter dildos.

For me, anal penetration creates an interesting set of sensations. First, the cold, gentle caress of lube being applied around the rim of my asshole. Then, a few seconds later, the gentle-yet- firm press of my lioness’ finger as she parts my puckered hole. That first intrusion is a little painful. I have to breathe and try to relax as she penetrates me. Mrs. Lion prefers using her bare fingers. If I ask, she will wear a glove. I know she prefers skin-to-skin contact.

Once she gets her finger fully inside me, she often leaves that there for a bit to allow me to get used to it. Then she will move her finger in and out. That motion is a combination of uncomfortable and exciting. I know my next anal visitor won’t be as easy to accept. Next, she will fill a little syringe with lube and insert it in my ass, releasing the lube inside. She may repeat this. When she’s satisfied that I’m slippery enough, she will lube the tip and body of a medium-sized butt plug. Then, with no further delay, I feel it pressing against me, sliding inside and stretching me. Initially, it’s not too bad. Before long though it starts to hurt.

Often, that means the lube had rubbed off and I was hitting a dry spot. Mrs. Lion will partially remove the plug, add a little bit more lube and continue pressing. Eventually, she reaches the shoulders of the plug where the diameter becomes much smaller. At that point I feel a sharp pain and then breathe a sigh of relief that the plug is firmly inside.

Often, this is where things end. She’ll leave the plug parked in my ass for a couple of hours, and then remove it and wipe away the lube. Other times, she will leave it in for a little bit and then remove it. She will then use one of my dildos and replace the butt plug with the silicone penis. This is followed by a slow in and out as she lets me get used to the feeling of being fucked.

This is always uncomfortable. If she leaves the dildos fully inserted it will begin to feel comfortable after a minute or two. Moving it in and out doesn’t really feel good to me. It isn’t so bad that I want her to stop. I just wish it would feel better. She picks up speed. It’s very intense for me. Sometimes she pulls the dildos all the way out and then immediately pushes it back in. At first, I really hate that sensationn. After she persists I start to get used to it. She picks up more speed pounding harder and pulling the dildos completely out after almost every stroke. I grunt and work hard to stay open and accepting. Sometimes I can’t and I ask her to slow down or stop. She usually listens to me.

In a way this is a problem. She reasons that she is doing this for me. So if I don’t like it and ask her to stop, she should do it. The reason that is something I would like to see changed is that I want to learn to be able to take it. There have to be times when I really want that discomfort to end. I know that if it does, I’m not going to learn. It would be easier for me if I didn’t have to avoid asking to stop. If my protests were ignored as a way of helping me grow, I think it would be a better experience for me.

We used to work on training me to take Mrs. Lion’s entire hand. We stopped. I would like to try that again. I read that some people use butt plugs a little differently. Instead of inserting them and leaving them in place, they use them in a similar way to how Mrs. Lion uses the dildos: they move it in and out forcing the anus to expand and contract with every stroke. This has to feel horrible at first, but I can see the value in this exercise. Forcing the expansion and contraction over and over is a very good way to train me to be able to relax more. If I can learn to just stay open, the in-and-out motion could become enjoyable. More importantly, learning to relax the anal sphincter muscles will make it much easier for me to accept Mrs. Lion’s hand.

I had a friend back east who was seriously into fisting men. No, she never had a chance to try fisting me. We talked about it once in a while and she told me that it normally takes about 45 minutes with a beginner. She didn’t use any tools. She just worked with her fingers. She claimed that by patiently and persistently working in one finger at a time, she could always get her entire hand up any man’s ass. I can see how it could take at least 45 minutes. My limited experience is that it takes patience to give me the time to relax at each step.

I don’t think I’ll ever be one of those guys who can get off while being pegged or fisted. I doubt I’ll even be able to get hard while that’s going on. But there’s something emotionally satisfying about having to learn to accept whatever Mrs. Lion chooses to insert. Even though I know I will be uncomfortable, I always feel closer to her after each session.

Lion's sling
This is our sling. It shares the dungeon with our waxing table (left) and our library. Note how high my legs are held by the restraints.
(Click image for a NSFW close up of me being pegged in the sling)

I realize that I miss insertion play. I don’t particularly like things up my ass, but I get aroused when I think of Mrs. Lion training me to accept larger dildos for eventual pegging. I actually get hard when I think about it. However, when she gets the lube out and tells me to roll over, there is no sense of anticipation.

For her part, she is usually clinical about how she goes about filling my ass. Occasionally, she will lube up a finger or two and manually explore my rear cavity. Usually, she uses her finger to lube my anus and then greases up the plug or dildo and slowly inserts it. She is always sensitive to my reactions and will stop or pull back a bit while I get used to the current stretch. She persists until I am fully penetrated.

Lion's dildo
This is where we left off when Mrs. Lion was working me up for pegging. The idea was that she could put this into our Rodeoh harness and she could go for it.
(Click image for a NSFW photo of it filling me)

Her favorite place for pegging is our sling. When I’m strapped in, I am fully exposed with my legs up and spread. My body is tipped so that the area between my legs is easily accessible. With my legs wide apart, my anus is fully available. I’m at a comfortable height for anal attention. This is a also her favorite place to work on my cock and balls.

Since our sling is in the basement dungeon, it requires effort to turn on the heat and then go down for activities. This effort is usually too much for her on a weeknight. Weekends are busy so we very rarely use our sling. It’s been several months since the last time I was in it.

That’s too bad. As you can see in this NSFW image (click here and here to view), my position in the sling makes me absolutely vulnerable to anything Mrs. Lion wants to do. My arms and legs are cuffed to the chains holding up the sling. When she pegs me, the sling rocks back and forth, essentially moving the dildo in and out using my own weight to drive it in and out.

The fact that I get turned on by thinking of this activity, yet when it is happening I feel uncomfortable and become soft is yet another contradiction in the way I process BDSM. This contradiction is probably why being anally stretched on a regular basis keeps me sexually aroused other times.

It sends a powerful message of control to me. Being strapped into the sling is very hot for exactly the same reason. Control is being taken from me. I get very turned on by that. Come to think of it, being locked into a chastity device is the same thing. It’s how I’m wired.

 

The thought occurs to me that Lion thinks too much. It’s possible he’s sabotaging himself. He may be so worried about my not getting any enjoyment out of the things we do that he can’t enjoy them either.

I’m not suggesting he should have enjoyed the figging and pegging yesterday. Mr. Weenie has reacted favorable in the past at times, but that doesn’t mean it always happens. And I really did a number on him this time. Actually, a few numbers. He expressed concern that I usually stop when he indicates he’s in pain. I don’t necessarily. In light of his concern, I decided to make an extra effort to convince him I don’t stop at the first sign of pain.

Once the big dildo was in and he was used to it (as much as he can be), I alternated between 50 short, quick strokes and 10 long, slow strokes. I saw him wincing so I know he was not having fun. Why did I decide 50 and 10? No idea. It just popped into my head so I did it. Did I have fun doing it? I wouldn’t call it fun but I figured it was a challenge for both of us as Lion suggested in his post. Can we top our high score of 50 short, quick strokes and 10 long, slow strokes next time? I guess we’ll find out.

I doubt his not being able to get hard can be blamed entirely on pegging or his overthinking. It’s quite possible he’s just in another slump. When we snuggle and he’s not aroused he tends to apologize to me. Maybe I should punish him when he apologizes. There’s really no need. I’d rather he tell me he’s not interested than having me try to no avail. I don’t want to make either one of us sore.

The bottom line is that I like doing things for him. It makes me happy to make him happy. I may not seem as receptive to playing sometimes but I think it’s normal for me to have slumps just like Lion has slumps. Of course his slumps make play impossible. Mine don’t have to.

[Lion – My slumps don’t make play impossible. My anus is always available to Mrs. Lion. I may not want a visit from the dildo, but that’s irrelevant.”]

Lion worked from home yesterday. He said he was freezing all day. He’s been wearing a sweatshirt around the house. I know he hates the sweatpants we got him to wear when he couldn’t wear a belt or suspenders after his surgery but I think he should be able to wear them around the house when it’s cold like it has been for the past week or so. Yes, there is a rule that he has to be naked in the house but I’m not heartless. Unless he considers making him wear the evil sweatpants being heartless.

By the time we snuggled he was nice and warm. He warmed me up. We didn’t play though. We were both tired. And snuggling is nice all by itself. At bedtime, however, Lion said he might be getting horny. It looks like we have plans for tonight!

If I remember, and Lion can help remind me, I could use some ginger on him. We go to the trouble of buying ginger and then we both forget it’s there. I’m sure Lion would rather have ginger in his ass than menthol (or worse) on his balls. The other day he wondered why I always put the menthol on his perineum where it hurts more. I told him I could put it on his ass if he’d rather. Nope. He didn’t. The reason I didn’t put it on his balls on Saturday was because I’d just shaved his balls and I’d nicked a few spots. The menthol would have been even worse if it hit those spots so I avoided the entire area. Sometimes I’m nice to him. [Lion – For the record, Mrs. Lion used a capsaicin rub on me; not menthol.]

For the record, I didn’t notice any difference in Lion’s erections on Saturday or Sunday. I do love when he’s super hard. I don’t know if he was and it didn’t register with me or what happened. I was just happy to be sucking him I guess. Then I got the bonus ejaculate. Yum!